m-Chloroperbenzoic acid → HCID 15027411, compound

HRID 1646697Notes

Reaction equation

HRID 1646697 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[CH2:5][S:6][C:7]1[NH:11][C:10]2[CH2:12][CH2:13][CH2:14][CH2:15][C:9]=2[N:8]=1.ClC1C=CC=C(C(OO)=[O:29])C=1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH3:1][N:2]([CH3:20])[C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[CH2:5][S:6]([C:7]1[NH:8][C:9]2[CH2:15][CH2:14][CH2:13][CH2:12][C:10]=2[N:11]=1)=[O:29]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 15027410HCID 15027410, compound

Product 1

HCID 15027411HCID 15027411, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

To a solution of 0.70 g (2.4 mmol) of 2-(2-dimethylaminobenzylthio)-4,5,6,7-tetrahydro-1H-benzimidazole in 7 ml of chloroform was added under chilling with ice 0.53 g (2.4 mmol) of 80% m-chloroperbenzoic acid for 10 min. To the resulting mixture were added chloroform and aqueous NaHCO3. The chloroform portion was taken out, and then subjected to extraction using six portions of 1N aqueous NaOH. To the aqueous NaOH portion was added an excess amount of aqueous NH4Cl to separate an oil out of the solution. The oil was then extracted with chloroform and dried over anhydrous sodium sulfate. Chloroform was distilled off, and the residue was crystallized from diethyl ether/hexane. The obtained crystalline products were collected by filtration and dried under reduced pressure to give 0.26 g of the desired compound as a white crystalline product, yield 35%.

Workup

  1. extractionsubjected to extraction
  2. additionTo the aqueous NaOH portion was added an excess amount of aqueous NH4Cl
  3. customto separate an oil out of the solution
  4. extractionThe oil was then extracted with chloroform
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationChloroform was distilled off
  7. customthe residue was crystallized from diethyl ether/hexane
  8. filtrationThe obtained crystalline products were collected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-6aed5c32f4e94f68b3856a975f9cb234
Source dataset
uspto-grants-1993_01
Patent number
US05180836

Reaction notes

Loading…